Ok, ALthough I do not think of myself as an old salt we have done a number of miles and passages, so for what is wirth heres my 0.02;

you really do not need a heavy displavement full keel boat for cruising.
keeping your systems simple pays off , no waiting for parts for yer refer etc.
Learn to sail your boat... you do need to be able to sail on and off an anchor without your motor, to heave to, etc etc. SAil your boat as if it were engineless.
IT does not cost anywhere near what you think it must to cruise, I was very happy on less than 200 a month, and as a couple we seem to be at about 300 a month ( plus boat maintenance)
Eat well- its important.
dont worry about the cosmetics, spend your time and money on the important systems.
COmfort is very very important, so make sure your boat is as comfortable as it can be, little luxuries like full length mirros do wonders for morale.
if you have to have a choice between insurance and equipment spend the money on way oversize anchors and chain ( lots of both)
you can never have too much line onboard
its meant to be fun, not an endurance contest, so always take the easy route.
Never buy a project boat thinking its a cheaper way into sailing- its not
Cruising you will very very rarely encounter truly heavy weather
its amazing how strong your realtionship will become after a few days at sea.